This is a very great question/post.
I was just talking with a (cis-male) co-worker about possible FFS, which I currently don't think about ever doing. (money and pain)
I do have different feelings about my face, depending on my mood, and also greatly depending on how a particular picture looks. When I look in the mirror however, I am much happier with what I see, although there are still a lot of masculine features. Since 2003 or so I only have 4 facial pictures (passport and business headshot) of myself. After coming out and transitioning I probably have 4 pictures per hour.

I am not currently using make up to hide masculine features and bring out more feminine looks because I am doing electrolysis every Wednesday, and don't want to have possible skin issues.
Most of the time I am okay with my looks, but for example at work, where of course I am 100% out, I am holding back on my femininity a little. At home I have two 11x14 headshot portraits framed in a 16x20 frame displayed on top and next to my 55 inch TV, with a portrait on my mom and me in between. Every time I go to sleep or feel a little down, I look at these and feel much better. One of the two portraits is my avatar here.
Mood, looks and how I see my face are directly related to one and another. What also helps me a lot is when I am shopping or somewhere out and about, and I hear people referring to me as a lady. (or woman, female pronounce etc.)
I think 80% of the time I feel okay about my face. (that's without makeup)